Hydrochloric Acid → 2-(3-Nitrophenyl)acetaldehyde

Temperature

100 °C

To a solution of 1-(2-methoxyvinyl)-3-nitrobenzene (1.8 g, 10.06 mmol) in THF (60 mL), was added 6N HCl (6.03 mL) and the mixture was heated at 100° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and the solvents were evaporated under reduced pressure to afford a solid. The solid was dissolved in EtOAc (45 mL) and water (50 mL) was added and the mixture stirred for 15 minutes. The separated aqueous phase was extracted with EtOAc (30 mL), and then the combined organic extracts were washed with 5% sodium bicarbonate (25 mL), brine (30 mL), dried (Na2SO4) and the solvents removed under reduced pressure. The crude compound was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane to afford the title compound (1.2 g, 90%).

1. temperatureto cool to room temperature
2. customthe solvents were evaporated under reduced pressure
3. customto afford a solid
4. extractionThe separated aqueous phase was extracted with EtOAc (30 mL)
5. washthe combined organic extracts were washed with 5% sodium bicarbonate (25 mL), brine (30 mL)
6. dry with materialdried (Na2SO4)
7. customthe solvents removed under reduced pressure
8. customThe crude compound was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane

ORD record

ord-a218a3f8ffd44953bc5fb54e008618ff

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716287B2